Are you afraid of dating someone your family doesn’t approve of? Are you tired of being uncomfortable with your own romantic life because of your culture’s restrictions on love and marriage? Do you wish you could date any age, religion, race, or culture you choose?

Welcome once again to The Art of Extraordinary Confidence, where today we’re going to be talking about how to find the inner confidence to reject your culture’s negative opinions, go after what you want, and create relationships with value.

For today’s episode, I’m going to go ahead and warn you right off the bat: it’s going to get controversial, and I’m going to push buttons.


Because it’s impossible to have an honest conversation concerning culture, religion, or race without using “trigger” words and picking apart the “rules” . . . and that’s always going to offend someone.

Now, some of what I reference here is based on a book I read a long time ago, called Compassion and Self Hate: An Alternative to Despair, by Theodore I. Rubin. It’s a very dense work by a brilliant psychoanalyst, but if you’re interested in this topic, I’d highly recommend it.

Within this book, the author discusses some of the biggest contributors to our self-hate—what he calls our “toxic culture.” Basically, it lays out the negative messages we receive day-in and day-out from our society or specific culture.

Now, even though every culture has some great ideas to share, they all have at least as many toxic ones . . . and it is our responsibility to notice the difference and reject the negative ones if we want to become our most confident selves.

Here’s an excellent example from one of my recent Mastermind calls:

There’s a man in the group who is in his forties and had spent years in a marriage that wasn’t working—in truth he was only staying in it for his kids. Eventually, with support from the group, he built up the confidence necessary to make the healthy life choice, and he ended the marriage. This ended up being not only beneficial for him, but also for his ex and their children—both members of the marriage are now thriving, and his relationship with his children has vastly improved.

In the meantime, he has also started dating again. He’s really opened himself up to seeing different types of women than he ever had before, and one of the criteria he loosened up on was age (he’s literally had dates with women 22-52 years old). Now, he currently has not intention of getting serious, and he’s being honest about that from the get-go.

Now . . . having heard that scenario, let me ask you this question: What is your initial reaction to the idea of a 40-something man dating a 22-year-old woman?

If you’re an American, I can almost guarantee that you’re uncomfortable with it at the very least.

Most of the time, when we have a cultural aversion to something, it’s because we have an unsavory story attached to it.

Consider the scenario of an older man dating a younger woman: in America, we assume it’s a case of the creepy old man taking advantage of the inexperienced, naïve woman.

But is that always, unconditionally the case?

What if I told you that, in this case, she had pursued him? What if I told you that he felt very unsure about that age difference himself at first, and even kept her at arm’s length?

In reality, this is simply a case of two consenting adults who are attracted to one another, have great conversation, and want to give each other a chance.

Does that sound so nefarious?

NO! And yet, he was shamed by a female work colleague who overheard him talking about it with a friend (and who knew absolutely nothing about their relationship).

So, who is right in this situation? Should two people suffer because this woman is uncomfortable with their mutual interest? Should he have listened to his own initial impulses and put the kibosh on it before it began?

Regardless of what your opinion is in this moment, he was able to walk away from the confrontation with this colleague . . . but it really bothered him.

Fact: the level to which you’re going to experience negative emotions about cultural shame is usually commensurate with the level to which you agree with it.

I like to think of it this way: if you don’t care about the rule, then you won’t care about people calling you out on it.

Let me use myself as an example. My wife and I are Burning Man hippies, so we really don’t have a problem with nudity. In fact, I think it’s something our culture focuses on WAY too much. In any case, since we feel this way, we let our boys run around naked whenever they want to. Sure, we get looks from people—and the occasional comment—but when someone at the beach gives us attitude, we pretty much shrug it off.

It literally doesn’t matter to us, because we think it is a bogus rule.

So, if you’re not totally clear on how you feel about specific rules, or if it’s never really come up for you (as in the case with the man from the example above), then you’re probably going to feel bad when someone shames you.

That is when you need to stop and take stock:

Do I feel bad because I can find some specific reason to feel bad, or do I feel bad because society says I’m bad and wrong?

If you keep running up against a road block after setting it up in that context, then it’s probably a sign that your reservations are the result of some cultural message that has no substance and doesn’t jive with your values.

Now, of course, I can see the other side of this argument: if a 45-year-old can date a 22-year-old, then what’s to stop a 40-year-old from dating a 17-year-old?

I get it, and that’s what these fears are based on—the fact that, at some point, it really DOES become a matter of someone taking advantage of someone else; it becomes a matter of slighting women who are the same age as these men; it becomes a matter of legitimizing the fixation of our culture with young women in porn and other “demeaning” contexts.

And the question with any of these cultural taboos really becomes, “Well, where’s the line?”

Let’s take some really blatant cultural taboos, like dating a cousin or eating a beloved animal, such as a horse or a dog.

Why can’t we date cousins? Well, beside the cultural aversion to family members becoming intimate, we also have a deeply ingrained fear of birth defects. When you take a look at actual statistics on “inbreeding” between cousins, however, the birth defect rates are infinitesimal. In fact, in many cultures around the world—and in European royalty for centuries—marriages between cousins is perfectly normal.

And what about eating dogs? In our culture, we keep them as pets, so we would NEVER eat them, right? Viewed logically, though, that taboo makes no sense: pigs are more intelligent than dogs, but we eat them; they have the same emotional capacity, but we don’t mind placing them in factory farming conditions—when it comes to slaughtering and consuming any living thing, what makes one animal any different from another, if not intelligence and emotional capacity? Is it because they have more personality? Maybe. But then we have to question the religious refusal of Hindus to eat cows.

Whatever the rule, we do what we have to do to justify it, but in the end, it’s all just obligatory cultural programming.

If you want to develop a higher level of confidence in every area of your life, you’re going to have to break free of cultural programming at some point or another.

Here’s the thing: you will never be able to discover you own true values and beliefs if you do not give yourself the freedom to question whether the culture you were born into conflicts with who you are as a human being.

Maybe your family has a problem with you dating someone of a different race, and yet, you value tolerance; maybe they will not abide you dating someone of another religion, and you value open-mindedness; maybe you believe that two people coming together from different backgrounds will create a deeper family connection because of the richness that different perspectives can provide.

Whatever your views, make sure that you give yourself the permission and the space to discover them.

There are a million different reasons why two people might find love—and frankly, as long as it’s not against the law, that’s between them and their god (figuratively speaking, of course). Most of these situations are context-dependent, so the next time you feel entitled enough to judge someone, ask yourself if that judgement is based on your culture or yourself.

That being said, it’s not up to anybody else to approve of your love life. As long as you’re within the rule of the law, then all you have to do is make sure that the relationship adheres to the parameters of your own values and that you have developed the confidence necessary to either defend those beliefs when questioned or brush off others’ judgements.

I could honestly discuss this topic for days, but since this isn’t a novel, let’s keep the conversation alive in the comments below. Have you ever felt judged by society for something you didn’t innately feel was wrong? Have your own cultural programming issues ever clouded your judgement regarding a family member’s choices? How do you work past these issues to maintain the important relationships to you that are steeped in culture? Let’s keep on pushing buttons and expand our views by sharing our rich cultural perspectives.

Until we speak again, may you have the courage to be who you are and to know on a deep level that you’re awesome.